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US6063543A Expired / Lapsed US ⏱️ 0.0 years remaining

Radiation-sensitive mixture and its use

Assignee: Siemens AG
•
Filing: 1999-04-26
•
Granted: 2000-05-16
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Expires: 2019-04-26
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Abstract

Abstract A radiation-sensitive mixture contains the following components: a film-forming polymer which has an acid-labile, hydrolysis-stable polymer unit and at least one thermally stable polymer unit; a radiation-sensitive compound which liberates an acid on exposure to radiation; a solvent; if required, additives. This radiation-sensitive mixture can be used for the production of positive or negative relief structures, in each case with an aqueous developer. The acid-labile polymer unit is a 1,2-dicarboxylic acid monoester and the theramally stable polymer unit is at least structure: ##STR1## x=Si or Sn y=O or NH

Inventors

  • 👤 Stefan Hien
  • 👤 Michael Sebald

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 20:34
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/0045; G03F7/075; G03F7/0757; G03F7/0758

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 384 words
A radiation-sensitive mixture including a film-forming polymer functionalized with 1,2-dicarboxylic acid monoester groups, comprising an acid-labile, hydrolysis-stable polymer unit (A) of structure: ##STR7## a thermally stable polymer unit (B) of structure: ##STR8## a second thermally stable polymer unit (C) of structure ##STR9## and a polymer unit (D) bearing reactive groups and having a structure ##STR10## in which the amount of (A) is from 1 to 99 mol %, the amount of (B) is from 1 to 99 mol %, the amount of (C) is from 0 to 50 mol %, and the amount of (D) is from 0 to 50 mol %, provided that the amounts of (A), (B), (C), and (D) total 100 mol %; and in which n=0, 1, 2 or 3; R 1 is a hydrocarbon radical bonded via a tertiary C atom to the O atom and having a total of 4 to 10 C atoms, or a 2-tetrahydrofuranyl or 2-tetrahydropyranyl radical; R 2 , R 3 and R 4 --independently of one another--are C 1- to C 6- alkyl or C 1- to C 6- alkoxy, C 6- to C 18- aryl or C 6- to C 18- aryloxy or aralkyl having a C 6- to C 18- aryl group and a C 1- to C 4- alkylene radical; R 5 is H or C 1- to C 6- alkyl; R 6 , R 7 , R 8 and R 9 --independently of one another--are H, C 1- to C 6- alkyl, C 6- to C 18- aryl, halogen, CN, methoxyphenyl or a radical of structure ##STR11## where R 15 is H, C 1- to C 6- alkyl, C 6- to C 18- aryl, CH 2 ═CH--, CH 2 ═CH--CH 2 --, or CH 2 ═CH--CO--; R 10 is H, C 1- to C 6- alkyl, C 2- to C 6- alkenyl, C 6- to C 18- aryl, halogen or halogen-substituted C 1- to C 6- alkyl; R 11 and R 12 --independently of one another--are linear C 1- to C 18- alkyl; R 13 and R 14 --independently of one another--are linear C 1- to C 18- alkyl or tert-butyl; X is Si or Sn, and Y is O or NH; a radiation sensitive compound liberating an acid upon irradiation, a solvent, and optionally at least one additive.
Claim 2
Dependent Claim 384 words
A radiation-sensitive mixture including a film-forming polymer functionalized with 1,2-dicarboxylic acid monoester groups, comprising an acid-labile, hydrolysis-stable polymer unit (A) of structure: ##STR7## a thermally stable polymer unit (B) of structure: ##STR8## a second thermally stable polymer unit (C) of structure ##STR9## and a polymer unit (D) bearing reactive groups and having a structure ##STR10## in which the amount of (A) is from 1 to 99 mol %, the amount of (B) is from 1 to 99 mol %, the amount of (C) is from 0 to 50 mol %, and the amount of (D) is from 0 to 50 mol %, provided that the amounts of (A), (B), (C), and (D) total 100 mol %; and in which n=0, 1, 2 or 3; R 1 is a hydrocarbon radical bonded via a tertiary C atom to the O atom and having a total of 4 to 10 C atoms, or a 2-tetrahydrofuranyl or 2-tetrahydropyranyl radical; R 2 , R 3 and R 4 --independently of one another--are C 1- to C 6- alkyl or C 1- to C 6- alkoxy, C 6- to C 18- aryl or C 6- to C 18- aryloxy or aralkyl having a C 6- to C 18- aryl group and a C 1- to C 4- alkylene radical; R 5 is H or C 1- to C 6- alkyl; R 6 , R 7 , R 8 and R 9 --independently of one another--are H, C 1- to C 6- alkyl, C 6- to C 18- aryl, halogen, CN, methoxyphenyl or a radical of structure ##STR11## where R 15 is H, C 1- to C 6- alkyl, C 6- to C 18- aryl, CH 2 ═CH--, CH 2 ═CH--CH 2 --, or CH 2 ═CH--CO--; R 10 is H, C 1- to C 6- alkyl, C 2- to C 6- alkenyl, C 6- to C 18- aryl, halogen or halogen-substituted C 1- to C 6- alkyl; R 11 and R 12 --independently of one another--are linear C 1- to C 18- alkyl; R 13 and R 14 --independently of one another--are linear C 1- to C 18- alkyl or tert-butyl; X is Si or Sn, and Y is O or NH; a radiation sensitive compound liberating an acid upon irradiation, a solvent, and optionally at least one additive.
Claim 3
Dependent Claim 28 words
The radiation-sensitive mixture according to claim 1, in which the radiation-sensitive compound which liberates an acid on exposure to radiation is an ionic compound, or a nonionic compound.
Claim 4
Dependent Claim 22 words
The radiation-sensitive mixture according to claim 2, in which the radiation sensitive compound is an onium salt or an imidosulfonic acid ester.
Claim 5
Dependent Claim 23 words
The radiation-sensitive mixture according to claim 1, in which the amount of the polymer unit (A) is from 5 to 50 mol %.
Claim 6
Dependent Claim 23 words
The radiation-sensitive mixture according to claim 1, in which the amount of the polymer unit (C) is from 1 to 50 mol %.
Claim 7
Dependent Claim 22 words
The radiation-sensitive mixture according to claim 1, in which the amount of polymer unit (D) is from 1 to 50 mol %.
Claim 8
Dependent Claim 15 words
The radiation-sensitive mixture according to claim 1, in which R 1 is tert-butyl or tetrahydrofuranyl.
Claim 9
Dependent Claim 10 words
The radiation-sensitive mixture according to claim 1, in which n=1.
Claim 10
Dependent Claim 26 words
The radiation-sensitive mixture according to claim 1, in which each of R 2 , R 3 , and R 4 is methyl and X is Si.
Claim 11
Dependent Claim 27 words
The radiation-sensitive mixture according to claim 1, in which each of R 6 , R 7 , and R 8 is H and R 9 is n-hexyl.
Claim 12
Dependent Claim 19 words
The radiation-sensitive mixture according to claim 1, in which polymer unit (D) is ##STR12## and R 10 is methyl.
Claim 13
Dependent Claim 38 words
The radiation-sensitive mixture according to claim 1, in which polymer unit (A) is ##STR13## polymer unit (B) is ##STR14## R 1 is tert-butyl, R 2 , R 3 and R 4 are each methyl and X is Si.
Claim 14
Dependent Claim 23 words
The radiation-sensitive mixture according to claim 12, comprising 50 mol % of polymer unit (A) and 50 mol % of polymer unit (B).
Claim 15
Dependent Claim 36 words
The radiation-sensitive mixture according to claim 1, in which the amount of polymer unit (C) is 10 mol %, R 6 , R 7 , and R 8 are each H, and R 9 is n-butyl.
Claim 16
Dependent Claim 50 words
The radiation-sensitive mixture according to claim 1, in which the amount of polymer unit (C) is 10 mol %, the amount of polymer unit (D) is 5 mol %, R 6 , R 7 , and R 8 are each H, R 9 is n-hexyl and R 10 is methyl.
Claim 17
Dependent Claim 19 words
The radiation-sensitive mixture according to claim 1, in which the solvent is cyclohexanone, ethyl lactate, or propylene glycolmonomethylether acetate.
Claim 18
Dependent Claim 52 words
A process of preparing a modifiable dual tonality resist structure in which a radiation sensitive mixture according to claim 1 is coated on a substrate, dried, imagewise irradiated, and heat treated under such conditions of temperature and time as determine the tonality of the image resulting from development in aqueous alkaline solution.
Claim 19
Dependent Claim 28 words
The process of claim 17 in which heat treatment is carried out at maximum 140° C. and a positive image is obtained after development in aqueous alkaline solution.
Claim 20
Dependent Claim 32 words
The process of claim 17 in which heat treatment is carried out at a temperature in excess of 140° C. and a negative image is obtained after development in aqueous alkaline solution.
Claim 21
Dependent Claim 18 words
A process according to claim 17 in which the resist structure obtained is modified by reaction with bis(aminoalkyl)oligodimethylsiloxane.

References Cited (Backward Citations)

US4491628A Cited
EP0388484A1 Cited
EP0394740A2 Cited
EP0395917A2 Cited
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US5346803A Cited
US5856071A Cited
GB2332679A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 2003-05-16 2003-11-15 2004-05-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2007-05-16 2007-11-15 2008-05-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2011-05-16 2011-11-15 2012-05-16 $7700.00 Window Closed / Lapsed

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